This Time Around
by IAmTheGrayArea
Summary: Based around Season 5, episode 4 - "The End" Dean finds himself in the future and learns that his Future self is sexually involved with Future Castiel.
1. Chapter 1

This wasn't Castiel.

Dean could tell immediately. For one thing Castiel would never be surrounded by this many attractive women – period, but _especially_ not while acting so suave and composed. Hell, Castiel was acting like _Dean_. And that alone was weird, really freakin' weird.

And what on earth was he wearing? What happened to his business suit and trench coat? I mean, that outfit just seemed to fit him, his personality. It was modest, conservative and sharp looking. That's right, damn it, that outfit looked good. But this earthy, dirty-looking shirt, what the hell was that?

"What are you a hippie?"

"You've gotten over trying to label me."

"Cas, we gotta talk—"

"Whoa, strange," Castiel responded, blinking a couple times.

"What?"

"You. You are not you… not now you anyway."

"No, yes, yes. Exactly."

"What year are you from?"

"2009."

Castiel sighed. "Who did this to you? Did Zachariah?"

"Yes."

"Huh, interesting."

"Oh yeah, it's freakin' fascinating. Now," Dean clapped his hands. "Why don't you strap on your angel wings and fly me back to my page on the calendar."

Turning, Castiel laughed to himself. "I wish I could just, uh, strap on my wings, but I'm sorry. No dice." He started to laugh again.

"What are you stoned?"

"Generally, yeah."

Dean inhaled slowly, studying Castiel up and down. "What happened to you?"

Castiel shook his head, raising his hands. "Life."

"So, what? You just sit around all day and smoke pot and have goddamn _orgies_?"

The ex-angel giggled quietly. "Well, I figured since I was cast out of heaven, why not just bask in the glory of sin? The women here…" His smile widened now. "Are fantastic creatures, one of God's greatest. And the men," he added, sort of like it was a tidbit of information that was so obvious that he didn't even need to say it.

Dean straightened his body. "Men?" His eyes darted around the room swiftly. "You mean… Are you… Did," Yep he couldn't finish the sentence.

Future Castiel gave him an odd look, but then a small smirk, almost sneaky it its secrecy, formed on his lips. "Oh, you don't… no I guess you wouldn't." He paused. "Yes, I have orgies of _both_ kinds." His smirk turned into a childish chuckle.

"Man, when you wanted to rebel against heaven, you really went for the kicker of all sins, huh?"

The former agent of heaven frowned. "No sin is greater than any other. That's just human weakness to make some sins more _acceptable_ than others. Plus, I don't think it really matters at this point." He glanced at the drug paraphernalia that was strewn across the floor. "Wanna hit?"

'_Hit_?' Did Dean just really hear Castiel use jargon for drug use? "Uh, no. I think I'll pass."

"C'mon," Future Castiel dragged the word out, pleading.

The Winchester brother shook his head. First off, never had he ever heard Castiel sound whiny (or pleading for that matter). And secondly, he was _not_being peer pressured by Castiel of all people. "God, this is loopy."

The now-human Castiel sat indian style on the floor, picking up a half-used joint and studying the tip before gripping a match. In a fluid, practiced movement Castiel dragged the match along the uneven boards and re-lit the joint. He pulled the smoke into his lungs, closing his eyes momentarily. "There are a lot of things you don't know about me," he said, allowing the smoke to bellow out of his mouth and the drug to constrict his throat.

"Well, after what I've seen here I'm pretty sure I don't want to know anything more about future you. It's fucking depressing, man."

Castiel shrugged. "Maybe."

And here Dean was willing to just let this go and make an effort to forget the conversation forever, but the way Castiel said 'maybe'—like he knew something that would be very advantageous for Dean to know, made the man rethink his indifference. He cocked his head and said, "Fine, I'll bite."

"No." Castiel waved his hand absently. "You probably don't want to know. Actually, I'm pretty sure you don't. And I'd probably be breaking some time continuum law by telling you this… you know, change the past you change the future type shit?" He scratched his head and sniffed heavily.

Dean grabbed the nearest chair and swung it over to his friend. He sat in it backwards. "Well now you're just being a tease. Tell me."

The words made Castiel laugh for some reason. "Alright." He stood and moved over to his bed. Climbing over it, he went to his nightstand and opened the drawer there. He picked up a garment and threw it at Dean. "He always forgets them in the morning."

It landed right in Dean's lap. He fingered it for a moment, recognizing them as boxers, but then—they weren't just any boxers. "Whoa." He looked up at Castiel.

"Red Calvin Klein boxers with a black elastic strap and a rip in the side from that knife attack with that deranged demon way back in the day," Castiel described without even looking at the undergarment.

Dean was frozen. He stared at the underwear in disbelief. These were _his_boxers, similar to ones he was wearing right now, in fact. "And by 'in the morning' you mean after a long meeting about how we're… you're going to kill Lucifer, right?"

"Sure," Castiel nodded. "A meeting that involves us both getting undressed and being on my bed. Whatever you want to think." He broke into a fit of giggles.

Dean didn't know which one was more disturbing, that he kept the same pair of underwear for five years or that his future self was fucking the future Castiel. He was pretty sure it was the underwear one because the other seemed… okay for some bizarre reason, almost like a should've-seen-that-one-coming moment.

"So you and my future self have sex every once in a while." God that was weird to say out loud.

"Try almost every night. Pretty much whenever he's not obsessing over Sam or trying to dodge women."

You mean, when _I_," he put up quotation marks, "stayed in Jane's cabin, I was actually…" he glanced at the bed.

"Here, yeah," Castiel confirmed, studying Dean intently.

"When did this start?"

"C'mon, Dean. You can't honestly deny that there's not a connection between you and past me."

"My Cas would –"

"_Your_ Cas?" The ex-angel grinned.

"_Past_ Cas is not like you. He would never do this." He pointed to his boxers.

"That's true. He would take more convincing, but," Castiel raised his hands. "It's not impossible."

"So future me started all this?"

"Yeah, but future you is a lot different now." For the first time there was sadness in Castiel's voice.

"How so?"

Castiel took a long drag. "You've hardened. You're detached at best, and when you're not you're angry and harsh. Not like you used to be." He sat back down, picking at his toes.

Outside the sound of an engine roared. A truck or large vehicle was approaching quickly.

"Speak of the Devil," Castiel snickered. "Wanna meet future you?"


	2. Chapter 2

Night had fallen on the camp and Dean found himself mentally lost and unsure. He had just had a bit of an altercation with his future self, who has turned out to be a grade A asshole, a topic that Castiel had described with a nice thick layer of sugar.

'_You've hardened_.'

Yeah! And become a torturer! Thanks for leaving that one out, Cas.

And now a calmness had settled everywhere and Dean had no idea what to do or where to go. Everything was so foreign, even the people there. The longer he stayed the more he hated this future. For one, the Apocalypse was well underway and most of the world's population had been wiped out, which was his fault. Secondly, his future self left much to be desired. How did he allow himself to get this way? More importantly, and what was bothering him the most about the future, was how he allowed Castiel to get like this. Obviously his future self cared for Castiel still, unless he was just using him for sexual gratification. The thought made Dean clench his teeth in anger. Castiel didn't deserve that. Dean would never do that to him, would he? He couldn't become someone so selfish and manipulative, but then, he _was_ capable of becoming someone clearly unrecognizable, so maybe his guess wasn't too far off the mark.

Castiel. Just thinking about him caused a surge of emotion to burn through Dean. Both pleasant and ill feelings were present within him, but he was tired of standing out in the middle of nowhere alone. He would go to Castiel's cabin and see what he was up to. Although this Castiel was different from his Cas, there still had to be something familiar in the ex-angel, something that would offer a sense of comfort for Dean.

He made his way quickly to Castiel's cabin. He had mentally remembered exactly where it was and he was about to amble right through the make-shift beaded doorway when he stopped short. Earlier when he just walked right in he almost interrupted what would have been an incredibly awkward moment. He did not want to see any type of weird sexual liaisons Castiel was involved in.

He held his breath and tried to listen as best he could for any indicators for him to turn his butt right around and find somewhere more suitable, but as he listened, he heard nothing. Nevertheless, he still took cautious steps through the beads and peeked into the room.

"Castiel?" he gruffly called out.

In response there was movement just around the corner and lo and behold Castiel lazily sauntered out, obviously stoned and very obviously half-naked. Dean's initial instinct was to jerk his eyes away because he had never seen this much of Castiel before and wasn't quite sure how to react. He felt heat circle his face and he darted his eyes back over to his friend.

A languid smile lay on the fallen angel's face. "I thought that you were _my_ Dean." The innuendo that was clear in his voice made the slight pink shade on Dean's cheeks mature into a deep burgundy.

Castiel let his eyes linger on Dean's face before laughing softly and turning away.

It was bizarre. The fallen angel's movements were different, almost as if it wasn't Castiel possessing Jimmy's body anymore but another entity. An entity that was the exact opposite of Cas. He was acting more… _human_. His actions were inelegant, so much different from his usual flawless and precise movements. His body was less fluid, almost imperfect in nature. And that's essentially what it was. He was imperfect now. Flawed.

"C'mon," Castiel said, reaching his hand out and brushing his fingers across Dean's bare arm. The former angel walked over to his bed and sat down.

That was officially the first time Castiel had _ever_reached out and touched Dean in a completely unnecessary way. Usually whenever they made physical contact it was when Cas was teleporting them somewhere or when Dean was in mortal danger, but never in a casual way like future Castiel just did. Dean studied his arm where Castiel's fingers had just been and a shiver ran through the area and the hunter tried to shake the feeling off. After a beat, he met his friend at the bed and sat down beside him.

Castiel was only wearing pants. They were loose kahki pants that hung very low on his abdomen. His feet were bare and so was his chest. His general bareness made Dean somewhat uncomfortable.

"I've got something you won't be able to deny," Castiel said, shuffling through his bedside drawer.

"If it's more of my future underwear I'm really not interested in—"

"It's not," Castiel confirmed, still sifting through items. "It's better. Ah-ha!" He tossed a small object out of the drawer and into his other hand. He held it close to the light on his bed stand before hovering it in front of Dean's face.

It was a tightly sealed bag of weed.

"Pot?"

"Not just _pot_, Dean. This is the best weed out there. I only share it with special people."

"Sounds like you've already had some tonight," Dean said.

Castiel shrugged, laughing boyishly. "Gotta past the time somehow."

"Uh, you seemed pretty busy earlier, you know, with the circle of women."

"Oh, that." Castiel waved his hand in dismissal. "Didn't follow through."

"Why not?"

"Oh, I don't know. I wasn't in the mood anymore, I guess." He packed a bowl as he spoke. "After you showed up I couldn't stop thinking about how you were here and about my Dean and how much he's changed." He fell quiet as he searched around for a lighter. When he found one he slowly licked his lips, bringing the bowl to his mouth.

Dean couldn't help but notice how Castiel's chest and stomach muscles tightened as he brought the drug deep into his lungs. Dean swallowed hard, inhaling sharply through his nose. He shouldn't be here. Not when Castiel was like this. What if Castiel tried to make a move on him? What if he responded to it? Because ever since he found out that his future self was really into future Castiel, he's started to feel some really weird feelings and it was beginning to freak him out.

"Here," Castiel said, nudging Dean's arm and offering over the bowl and lighter.

Using drugs probably wasn't the best choice of action if Dean wanted to stay in the right mindset, but he lit up the bowl anyway. He didn't know why. Castiel wanted him to and that seemed like enough. He didn't smoke much so it was a little awkward maneuvering the bowl into the right place and working the lighter, but Castiel was more than willing to assist.

"Here, let me," Castiel said, taking the lighter and scooting closer. Now his leg was touching the side of Dean's hip and leg. Again Dean swallowed hard. "Put it to your lips."

Dean did and Castiel hung the lighter over the bowl.

"When I light it, start to inhale slowly and for as long as you can." The ex-angel's voice was low and soft. His thumb ignited the lighter and the weed burned brightly.

The hunter inhaled and the drug burned as it traveled down his throat and into his lungs. He did as told, holding it for as long as he could and when he couldn't any longer he allowed the smoke to expel from his mouth.

Castiel watched him closer, a half smile settled on his face. "Good. That was good." With quick proficiency, he brought the bowl back to his lips and took a quick hit. He held it for a couple seconds and then placed the paraphernalia on his bedside table and turned to Dean. He motioned for Dean to come closer. When Dean only minutely responded, Castiel lifted his hand to the side of the hunter's chiseled face and brought him in so close that their faces were almost touching.

Dean stiffened greatly and Castiel sensed it. The former angel let his fingers gently travel under the hunter's chin and his mesmerizing blue eyes looked so deep into Dean's that Dean knew that he should just relax and trust Castiel. He allowed his shoulders to loosen and he looked back comfortably into his friend's eyes.

Castiel tilted his head and just barely brushed his lips across Dean's and the hunter responded by parting his lips slightly. Having held the drug in his lungs this entire time, Castiel finally exhaled, softly sending the smoke through Dean's mouth and down into the other's lungs. They both closed their eyes and felt the smoke and breath being exchanged between them. Castiel let his hand travel down Dean's neck and to his shoulder but he stopped there.

The drug was consuming Dean's brain and he felt his… _need_escalating at the heat and closeness of his friend.

When the smoke ran out, Castiel lingered over Dean's lips for a moment, the want was palpable between them, but then Castiel pulled back slowly.

Dean watched the other man pull away and it pained him tremendously. Castiel couldn't just tease him like that. He wanted more. He _needed_ more. The further away Castiel was, the unhappier he became and he knew exactly how to fix it.

Very commandingly, Dean shot his hand out and gripped the back of Castiel's neck, forcefully bringing their lips truly together.

Castiel somewhat awkwardly fell into the other man's lap, but recovered quickly, inhaling sharply through his nose as he responded against Dean's lips. He swung one of his legs over Dean's body so that he was straddling him.

The hunter's hands were all over the other's smooth, warm bare skin, cupping beneath his friend's body, pulling him closer than seemed possible, while Castiel's hands were maneuvering through Dean's hair. Their hips were close, so very close and Castiel let a quivering exhale escape into Dean's mouth.

"Your touch," Castiel breathed, feeling Dean's lips travel down his neck, sucking lightly. "Is different than my Dean's. It's softer. More loving… better." His last word was almost nothing more than a breath of air.

Dean used his strength to swing Castiel around so that Castiel was on his back, laid out across the bed. The hunter crawled up the other man's body, kissing up Castiel's abdomen and then chest and then neck and finally back to his amazing lips. Soft and supple and very agreeably responsive beneath his own. Dean felt some stubble rub against his lips and face and it was so strange and different but in a good way.

Castiel's pants were thin and Dean could feel the former angel's hardening area against his stomach and felt his own area respond swiftly, tightening and pulsing.

"I miss this," Castiel said quietly. "I miss you."

"But you have me, right? Future me?"

"No," Castiel answered. "We stopped doing this and started just… fucking. There's no more compassion, just lust."

It's true. His future self did not seem like the warm and fuzzy type, and just thinking about the future Dean and Castiel's relationship made him really appreciate the connection he had with his Cas. But then, the two in the future once had what Dean and his Cas had, so what's to say that he and his Cas wouldn't go down the same road? Man, Dean shook his head softly. This was getting confusing.

Dean thought about his Cas. His angel would never become like this, and the hunter laughed softly as he remembered that time he took Cas to a brothel to try and get him lucky, but Cas was too terrified to even talk! Cas would never—but then a hard realization hit Dean. This was Castiel. This spun out hippie lying before him was _his_ Cas. He had just become damaged, so damaged. He had experienced the cruelties of life and had been buried and corrupted by them. He had been vulnerable and he wasn't prepared enough to deal with the darkness of humans and he lost. He was ruined. He was strong in so many ways but not when it came up against human nature.

And Dean had allowed it to happen.

A mixture of pure sadness for Castiel and immense anger for himself tangled within Dean and his instinct was to pull Castiel closer to him and apologize with his touch, with his kiss. But not even that was enough, nothing was enough to receive forgiveness for what he had allowed to happen, but he needed to apologize anyway.

"I'm sorry, Cas. I'm so sorry," he whispered on the side of Castiel's face.

Castiel shifted beneath the hunter, opening his legs and wrapping them around Dean so that his bare feet rubbed back and forth against the backs of Dean's calves. "Dean," he whispered back. "Fix me."

The hunter responded with a small moan. "I will, Cas. I will."

Cas dug his fingers into Dean's back and thanked the man with a eager and deep kiss. And they did this for a while, until they got to the point where it was expected to move beyond kissing and beneath the clothes.

It was then that Dean forced himself to pull away. "I can't, Cas." He sat up and Castiel closed his eyes, but did not reach out to the hunter. "My future self may take advantage of you like this, but I can't. I want to do this, but I want to do it right."

"Right, how?"

"With you, but with past you. _My_ you. If I protect you in the past and do this right, then hopefully neither of us will end up like we are here."

Silence settled between them and Castiel let out a long sigh. Finally he spoke. "Okay." He swallowed and licked his bottom lip. "You're right." He wasn't angry, but he didn't disguise the disappointment he felt.

Dean maneuvered back to the edge of the bed and Castiel sat up as well, putting his hand on Dean's shoulder and squeezing. "You can do it, Dean. Save me. Save yourself. Save the world."

"Already failed once, but this… seeing you and what the world has become. I have to stop it. I will stop it."

A creak from one of the wooden floorboards brought both men's attentions toward the beaded door. Future Dean stood there, staring at the two of them.

"Sorry," he said sarcastically. "I didn't mean to interrupt." He turned and left without another word.

"Dean," Castiel called out, getting up from the bed, but the present Dean stopped him.

"Hold on. I'll talk to him."

Dean caught up with himself not too far away from the cabin. "Hey! Hold on."

Future Dean turned back around. "What?"

"You're mad. I get it. You can be mad at me all you want, but do not take this out on Cas. You have no right. No right!"

"Oh, really?"

"Yes, really, you cold son of a bitch. You let him get like this. _You_ did! There is no one else to blame and so you better start taking care of him because _you know_he's the best thing in your life. You've let everything else slip away, don't you dare let him!"

Future Dean cleared his throat but did not respond. Instead he walked past present Dean and made his way back over to Castiel's cabin and went inside.

Dean followed, going up to the door and listening.

"You shouldn't be surprised. Past you is who I fell in love with." It was Castiel's voice.

Future Dean responded but his voice was too low to distinguish singular words.

There was some movement within the room and the springs on the bed squeaked as if one or both had sat on the mattress.

"Wouldn't you want that?" Castiel again.

Dean's response was short.

And then there was very little noise. So little, in fact, that present Dean's curiosity rose so much that he peeked his head around the corner and found both men on the bed. Future Dean had Castiel locked in a deep kiss. It looked gentle and loving. They pulled away and some whispers were exchanged and Castiel smiled, letting his hand rest on the back of Dean's neck.

Future Dean let his hand drop and his fingers started working at the knotted string that held Castiel's pants up. The string loosened easily and Dean slipped his hand beneath the layer of cloth.

Present Dean nodded. He was satisfied with the way the scene unfolded, and as he watched it was _unfolding _pretty quickly so he slipped back out, not wanting to see anything more.

Dean figured that hopefully he would be experiencing his own fair share of personal moments with his Cas.

* * *

And then everything changed. Dean felt the sensation of falling and his stomach turned unpleasantly. His feet hit solid ground unexpectedly and he was out on the side of a street in the middle of the night.

He turned suddenly and found a sight so appealing that he almost reached out and hugged the angel standing before him. "Pretty nice timing Cas."

"We had an appointment," Castiel responded in his perfectly-logical, freaking sexy way.

In that moment Dean knew that he'd do it right this time. Now he had the chance. He wouldn't let Castiel break like he did before. He would take care of him.

Reaching out, Dean placed his hand on Castiel's shoulder. "Don't ever change."

Softly, the hint of a smile appeared on Cas's lips.

Yep, Dean nodded inwardly. He loved him. He loved that damn angel so much. He'd just have to show him.


End file.
